[4+2] cycloaddition reactions of 4-sulfur-substituted 2-pyridones with electron-deficient dienophiles

被引：33
作者：
Chou, Shang-Shing P. [1 ]
Wang, Hui-Chen [1 ]
Chen, Pong-Won [1 ]
Yang, Chun-Han [1 ]
机构：
[1] Fu Jen Catholic Univ, Dept Chem, Taipei 24205, Taiwan
来源：
TETRAHEDRON | 2008年 / 64卷 / 22期
关键词：
2-pyridones; 4+2] cycloaddition reactions; Diels-Alder reactions; isoquinuclidines;
D O I：
10.1016/j.tet.2008.03.030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[4+2] Cycloaddition reactions of 4-(phenylthio)-1-tosyl-2-pyridone (6a) and 4-(phenyisulfonyl)-1-tosyl-2-pyridone (6b) with electron-deficient dienophiles 7 (N-methylmaleimide, N-phenylmaleimide, and methyl acrylate) gave new isoquinuclidine products 8-10. The N-tosyl group of 6a and 6b was also efficiently converted to N-alkyl derivatives 6c-f, which showed different stereoselectivity toward reactions with dienophiles 7. Several other dienophiles 15 (dimethyl acetylenedicarboxylate, methyl vinyl ketone, ethyl vinyl ether, and methyl methacrylate) were found not to react with 6a or 6b, but led to the formation of tosyl migration products 4-(phenylthio)-O-tosyl-pyridinol (16a) and 4-(phenylsulfonyl)-O-tosyl-2-pyridinol (16b), respectively. The reactivity, regioselectivity, and stereoselectivity of the cycloaddition reactions were also compared with semi-empirical calculations. (C) 2008 Elsevier Ltd. All rights reserved.
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收藏
页码：5291 / 5297
页数：7
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